100,000+ ROAD TRIPS SOLD
Guess Where Trips
Mystery, one-day, self-guided road trips.
Four surprise stops on every road trip.
Handpicked and well-researched road trip stops.
Spooky options for those craving an eerie day out.
130+ road trips to choose from in Canada and the USA.
Eight haunted road trips to choose from!
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100% Money-Back Guarantee
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AS SEEN IN
Redefining Road Trips
Mystery Road Trips for the Paranormal Lover
Ghost Stories
Learn about the ghosts and ghouls that haunt buildings.
Haunted History
Detailed and interesting history on the sites you're visiting.
Spooky Stops
Odd occurances witnessed by paranormal experts.
Historic Buildings
Historic and abandoned buildings with chilling pasts.
Had the absolute best time with my best friends on this trip - it was spooky vibes but fall ambience, and every stop was a lot of fun to walk around and explore.
Miranda M.
Verified Buyer
There were places we would have never found and some very interesting history. No ghost sightings but we did hear some strange voices of two women talking at one of the outdoor stops and there was no one around for miles.
Kim G.
Verified Buyer
I've been to these areas before but never knew about these haunted stories. SO COOL. I hope they launch another haunted trip in the area. Can't wait to try another one.
C.
Verified Buyer
Frequently Asked Questions
What is Guess Where Trips?
At Guess Where Trips®, we specialize in self-guided one-day surprise road trips. Leave the stress of planning to us! We design each road trips around a general theme, so you will have an idea of what you might get up to during the day, but you won’t know where we’re sending you! We love finding new small businesses, hidden gems, cute cafes, and picturesque towns.
How do I know where I'm going?
Our road trips are intended to be surprises, but there are a few ways to get a better idea of where you'll be going:
1. Check out our Trip Map! This allows you to see the general area of where each trip ends.
2. Frequently Asked Questions: Each trip has its own set of frequently asked questions. These are located bottom of the specific trip page. Please read this section for a list of approximate round-trip driving distances from nearby cities.
3. Ask us! We're always here to help with any questions you might have. Start a chat with us or send us an email with your departure area and travel interests, and we'll send you our trip recommendations.
What is the difference between a mailed trip and a PDF trip?
Mailed Trip: This is most popular option. With a mailed trip, you will receive 5 sealed envelopes including 4 well-curated surprise stop envelopes and a “Before You Go” envelope which will give you just the right amount of details, without ruining the surprise stops. On the day of your road trip, your surprise stops will be revealed to you as you open each envelope.
PDF Trip: These are great for road trippers who don’t want to wait for their package in the mail. Our PDF trips are the same road trip as the mailed option just in a digital format. Once you purchase a PDF trip, you will receive an email with a link to download your trip.
What is included in my package?
Your road trip includes a well-curated itinerary for the day with a focus on small businesses, cute shops, hidden gems, and unique locations.
What's not included: Food, drinks, gas, and admission (if there is a fee!) are not included in the price of our trips.
How long are your road trips?
Our road trips are designed to be one day trips. Each trip takes roughly 6-8 hours to complete - this includes time spent at the recommendation and driving.
In the Before You Go booklet, we will tell you what time we recommend leaving for your road trip. Keep in mind that the later you leave, the less time you may have to spend at each stop.
Will I see a ghost on the haunted trips?
To be completely honest: no. These trips are about haunted history and chilling tales, and not so much about the likelihood of encountering something paranormal.
